KR101335906B1 - Curable organopolysiloxane composition, sealing material for flat panel display comprising the same and flat panel display device - Google Patents

Abstract

The present invention provides a curable organopolysiloxane composition that cures at room temperature and under ultraviolet irradiation and has excellent adhesion and release properties.

(A) 100 mass parts of organopolysiloxane which is a condensation reaction product of 100 mass parts of (I) component (1) and 200 mass parts of (II) components, (B) (meth) acryl-functional alkoxy represented by following General formula (1) 1-50 mass parts of silane, (C) 0.01-10 mass parts of catalysts for condensation reaction, and (D) 0.01-10 mass parts of photoinitiators.

≪ Formula 1 >

Organopolysiloxane Compositions, Flat Panel Displays

Description

Curable organopolysiloxane composition, the sealing compound for flat panel displays containing the same, and a flat panel display element TECHNICAL FIELD [CURABLE ORGANOPOLYSILOXANE COMPOSITION, SEALING MATERIAL FOR FLAT PANEL DISPLAY COMPRISING THE SAME AND FLAT PANEL DISPLAY DEVICE}

BRIEF DESCRIPTION OF THE DRAWINGS It is a figure which shows the aspect which uses the sealing compound for flat panel displays of this invention for a flat panel display element.

BRIEF DESCRIPTION OF THE DRAWINGS FIG.

2: glass substrate

4: electrode

8: film circuit

20: seal area

[Patent Document 1] Japanese Patent Publication (S) 53-36515

[Patent Document 2] Japanese Unexamined Patent Publication No.

TECHNICAL FIELD The present invention relates to a curable organopolysiloxane composition that is cured at room temperature and ultraviolet light, and particularly preferably a curable organopolysiloxane composition suitable for use in coatings for electrical and electronic components and their circuits, and sealants for flat panel displays, and flat plates comprising the same. A sealing compound for displays and a flat panel display element.

Conventionally, various are known as room temperature curable silicone rubber composition (henceforth "RTV") which provides a rubbery elastomer at room temperature. Cured rubbers obtained from RTV are used in various fields because they have excellent weather resistance, durability, heat resistance, cold resistance, etc., compared to other organic rubbers, and in particular, in the construction field, glass-to-glass adhesion, metal-to-glass adhesion, and concrete joint It is widely used for uses, such as a seal.

Moreover, there exists a tendency for a dealcoholization type RTV to be used abundantly in the point of adhesiveness with respect to to-be-adhered bodies, such as an epoxy resin, as an adhesive and coating agent for electrical and electronic components. Similarly, dealcohol type RTVs are used abundantly as sealants in flat panel displays, which are rapidly increasing in volume.

By the way, with the speed up of the production line of an electrical and electronic industry, improvement of the hardening speed is calculated | required about the curable composition used as a sealing compound etc. in these lines. Accordingly, an ultraviolet curable organopolysiloxane composition having a faster curing rate than conventional silicone rubber curable compositions such as condensation type, heat curing type, and platinum addition reaction type has been developed. For example, the composition containing an acryl-group containing polysiloxane and a sensitizer is proposed as this ultraviolet curable composition (refer patent document 1).

However, in this composition, in order to obtain the hardened | cured material of a rubbery elastomer, it is necessary to use a high molecular weight linear polymer as a base polymer. For this reason, the amount of the acryl group located at the terminal of the organopolysiloxane is relatively very small, the curability is lowered, and there is a drawback that the surface portion in contact with air in the composition hardly hardens due to inhibition of oxygen hardening. . Therefore, as this kind of photocurable composition, only the resin phase with a relatively large amount of acryl groups is put into practical use, the cured product obtained is inferior in tensile strength, and there existed a problem that the composition itself also lacks storage property.

To remedy this drawback, the present inventors first propose a composition combining a novel compound called alkoxy-α-silyl ester with a (meth) acryl functional alkoxysilane, a divalent tin-based compound, a photopolymerization initiator, and a curing catalyst. (See patent document 2).

However, in the case of the composition described in Patent Document 2, there is an advantage of providing a practical silicone elastomer as a cured product, but there is a problem that the adhesion of the cured product to glass or metal is insufficient, and it is proved to be unsuitable for various adhesive applications and seal applications. It became.

On the other hand, recently, in the seal of a region including an electrode on a glass substrate of a flat panel display panel and a film circuit connected to the electrode, it is necessary to remove the cured product used in the seal from the panel substrate for repair or repair of the finished panel. At this time, it is required that the cured product can be interfacially peeled from the surface of the substrate and not remain on the surface.

However, in the prior art, hardened | cured material which does not remain on the surface by interfacial peeling from the surface of a base material was not developed. For example, in order to improve the adhesiveness to the glass and metal of the composition of patent document 2, it is assumed to add the organosilicon compound which has an amino group or an acryl group, but when it does so, a composition adheres to a base material and the surface of a base material at the time of peeling Cured product remains.

Accordingly, an object of the present invention is a curable organopolysiloxane composition which can be cured under room temperature and ultraviolet irradiation to form a cured product having good storage stability and having excellent adhesion and release property with respect to glass, metal, plastic, and the like, and a flat panel display including the same. A sealing compound for use and a flat panel display element are provided.

That is, in order to achieve the said objective, curable organopolysiloxane composition of this invention is organopolysiloxane 100 which is a condensation reaction product of (A) 100 mass parts of following (I) components, and 1-200 mass parts of (II) components. parts by weight [stage (I) component is R ₃ SiO _1/2 units (wherein, R represents a group each independently unsubstituted or 1, the number of 1 to 6 carbon atoms, a substituted hydrocarbon group) and SiO _4/2 units a repeating unit and, SiO _4/2 units for 1 mole of R ₃ SiO _{1 /} a ratio of ₂ units of from 0.5 to 1.2 mol, and SiO _4/2 units per 1 mol of R ₂ SiO _2/2 units and RSiO _{3 At least one of / 2} units (wherein each independently represents an unsubstituted or substituted monovalent hydrocarbon group having 1 to 6 carbon atoms), each unit is 1.0 mol or less and the sum of each unit is 1.0 mol It may have to be below, and has less than 6.0 mass% of the hydroxyl group couple | bonded with the silicon atom. Organopolysiloxane, (II) component is diorganopolysiloxane whose molecular chain ends are blocked with a functional group-containing silyl group, (B) 1 to 50 parts by mass of (meth) acryl functional alkoxysilane represented by the following formula (1), 0.01 to 10 parts by mass of the catalyst for condensation reaction, and 0.01 to 10 parts by mass of the photoinitiator (D).

(Wherein R ¹ is a hydrogen atom or a methyl group, R ² is a divalent organic group, R ³ and R ⁴ are the same or different unsubstituted or substituted monovalent hydrocarbon groups, respectively, a is an integer of 0 to 2).

It is preferable that the said (II) component is diorganopolysiloxane represented by following General formula (2).

(In formula, R <^5> is respectively independently unsubstituted or substituted C1-C10 monovalent hydrocarbon group, X is each independently a functional group, a is an integer of 1-3, n is an integer of 10 or more.)

The sealing compound for flat panel displays of this invention contains the said curable organopolysiloxane composition.

The flat panel display element of this invention uses the said sealing compound for flat panel displays for the sealing of the area | region containing the electrode on the glass substrate of the said display, and the film circuit connected on this electrode.

BEST MODE FOR CARRYING OUT THE INVENTION [

Hereinafter, the water repellent composition which concerns on embodiment of this invention is demonstrated. The water repellent composition of this invention contains the following (A)-(D) component as an essential.

[(A) component]

(A) component improves adhesiveness to a to-be-adhered body, and the strength of hardened | cured material, and consists of organopolysiloxane which is a condensation reaction product of 100 mass parts of following (I) components, and 1-200 mass parts of (II) components.

(I) component and an R ₃ SiO _1/2 units (in the formula, R each independently represents an unsubstituted or represents a 1 of 1 to 6 carbon atoms optionally substituted hydrocarbon group) and SiO _4/2 units as the repeating unit .

Examples of R include alkyl groups such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, iso-butyl group, tert-butyl group, pentyl group and hexyl group; A cycloalkyl group such as a cyclopentyl group and a cyclohexyl group; Alkenyl groups, such as a vinyl group, an allyl group, an isopropenyl group, butenyl group, a pentenyl group, and a hexenyl group: Aryl groups, such as a phenyl group: Chloromethyl group, 3-chloropropyl group, 1-chloro- 2-methylpropyl group, 3 Halogenated alkyl groups, such as a 3, 3- trifluoro propyl group, etc. are mentioned, A methyl group, a vinyl group, and a phenyl group are especially preferable, and a methyl group is the most preferable. Each R may be a separate group or may be the same group.

(I) a SiO _4/2 R ₃ SiO ratio of _1/2 units to the units of 1 mol of 0.5 to 1.2 mole is required and, preferably, in the range of 0.65 to 1.15 mol of the component. R ₃ a SiO ratio of _1/2 units is strength of the cured product obtained is less than 0.6 mol becomes insufficient and when it exceeds 1.2 mole will drop the cured transparent. When transparency of hardened | cured material is inferior, UV light will become hard to reach the core part of hardened | cured material, and core part hardenability will fall.

Further, SiO _4/2 units of R ₂ with respect to 1 mol of SiO _2/2 units and RSiO _3/2 unit (each formula, R is a number from 1 to 6 carbon atoms unsubstituted or substituted independently in the (I) component Or a monovalent hydrocarbon group) may be provided so that each unit is 1.0 mol or less, and the total of each unit is 1.0 mol or less. More preferably, R ₂ SiO _2/2 units, and each unit is from 0.2 to 0.8 mole of RSiO _3/2 units, and the total of the unit is less than 1.0 molar.

Such mixing ratio is, the R ₂ SiO _2/2 units of a combination of 0.2 mole and 0.7 mole of RSiO _3/2 units and the like with respect to SiO _4/2 units per mol.

In the (I) component, R ₂ SiO _2/2 units and RSiO _3/2 If it is not containing one or more of the units of the composition is a resin, it tends to be rather different from the solution prior to curing that the workability decreases. On the other hand, when R ₂ SiO content of each unit of the _2/2 units and RSiO _3/2 units exceeds 1.0 mole, or, the total amount of the unit exceeds 1.0 mole, the transparency of the composition tends to drop.

In (I) component, it has less than 6.0 mass% of hydroxyl groups couple | bonded with the silicon atom of the said each unit. A hydroxyl group is produced when the component (I) is produced by a cohydrolysis / condensation reaction, and is bonded to a silicon atom. A hydroxyl group is necessary for condensation reaction of (I) component and the following (II) components, and it is preferable that the minimum is 0.1 weight% or more. Preferably the content of hydroxy groups is from 0.2 to 3.0% by weight. When content of a hydroxyl group is 6.0 weight% or more, the hardness of the obtained hardened | cured material will become high too much and adhesiveness will fall. Moreover, when content is less than 0.1 weight%, the intensity | strength of the obtained hardened | cured material may become inadequate.

(I) A component can be obtained by a well-known method, For example, the alkoxy group containing silane compound corresponding to each said unit can be condensed by co-hydrolysis in an organic solvent, and can obtain what is substantially free of a volatile component. have.

As a specific method for obtaining the component (I), for example, R ₃ SiOMe and Si (OMe) ₄ may be covalently added in an organic solvent with R ₂ Si (OMe) ₂ and / or RSi (OMe) ₃ as desired. It can decompose | disassemble and condense (In each formula, R represents an unsubstituted or substituted C1-C6 monovalent hydrocarbon group each independently, and Me represents a methyl group.).

The organic solvent is preferably one capable of dissolving the organopolysiloxane produced by cohydrolysis and condensation reaction, and typically includes toluene, xylene, methylene chloride, naphtha mineral spirit, and the like. have. In addition, without using the said organic solvent, you may use the diorganopolysiloxane whose viscosity in 23 degreeC is 20-2000 mm <2> / s instead of the following (II) component.

About the content molar ratio of each unit with respect to (I) component, it can set suitably by adjusting the injection molar ratio of the methoxysilane compound corresponding to each unit, for example.

In addition, content of the said hydroxyl group in (I) component can be changed by adjusting the conditions of co-hydrolysis and condensation reaction.

Component (II) is diorganopolysiloxane whose molecular chain ends are blocked with functional group-containing silyl groups, and component (II) is condensed with component (I).

The functional group is not particularly limited as long as it is condensation-reacted with a hydroxy group bonded to the silicon atom of the component (I). Examples of the functional group include a hydroxy group and an alkoxy group such as a methoxy group, an ethoxy group, a propoxy group and a butoxy group; An alkoxyalkoxy group such as a methoxyethoxy group, an ethoxyethoxy group, or a methoxypropoxy group; Alkenyloxy groups such as vinyloxy group, isopropenyloxy group and isobutenyloxy group; Ketoxime groups, such as a dimethyl ketoxime group, a methyl ethyl ketoxime group, a diethyl ketoxime group, and cyclohexane oxime; Acyloxy groups such as acetoxy group, propionyloxy group, butyryloxy group, octanoyloxy group and benzoyloxy group; Aminooxy groups such as N, N-dimethylaminooxy group and N, N-diethylaminooxy group; An amino group such as a dimethylamino group, a diethylamino group, a butylamino group, and a cyclohexylamino group; Hydrolysable groups, such as amide groups, such as an N-methyl acetoamide group, an N-ethyl acetoamide group, and an N-methyl benzamide group, are mentioned, Preferably they are a hydroxyl group and an alkoxy group, Especially preferably, they are a hydroxyl group.

It is preferable that (II) component is diorganopolysiloxane represented by following General formula (2).

(2)

(In formula, R <^5> is respectively independently unsubstituted or substituted C1-C10 monovalent hydrocarbon group, X is each independently a functional group, a is an integer of 1-3, n is an integer of 10 or more.)

As R ⁵ , for example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, iso-butyl group, tert-butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, Alkyl groups such as decyl groups; A cycloalkyl group such as a cyclopentyl group and a cyclohexyl group; Alkenyl groups such as vinyl group, allyl group, isopropenyl group, butenyl group, pentenyl group and hexenyl group; Aryl groups such as phenyl group, tolyl group, xylyl group and naphthyl group; Aralkyl groups such as benzyl, phenethyl, and phenylpropyl groups; And halogenated alkyl groups such as chloromethyl group, 3-chloropropyl group, 1-chloro-2-methylpropyl group, and 3,3,3-trifluoropropyl group, and the like, and among these, a methyl group is preferable.

As X, the above-mentioned functional group can be used, for example.

In the formula (2), n is an integer of 10 or more, but the viscosity of the diorganopolysiloxane (component (II)) at 23 ° C. is 300,000 mm 2 / s or less, preferably a number which becomes a fluid in the range of 100 to 100,000 mm 2 / s. desirable.

As a specific example of the diorganopolysiloxane represented by the said Formula (2), For example, molecular chain both terminal silanol group blocking polydimethylsiloxane, molecular chain both terminal silanol group blocking dimethylsiloxane, methylphenylsiloxane copolymer, molecular chain both terminal trimes Methoxy siloxy group blocking polydimethylsiloxane, molecular chain both terminal trimethoxysiloxy group blocking dimethylsiloxane, methylphenylsiloxane copolymer, molecular chain both terminal methyldimethoxysiloxy group blocking polydimethylsiloxane, molecular chain both terminal triethoxysiloxy group Polydimethylsiloxane etc. are mentioned. These may be used alone or in combination of two or more.

<Condensation Reaction of Component (I) and Component (II)>

Component (A) is 1 to 200 parts by mass of component (II), preferably 5 to 150 parts by mass of component (II), particularly preferably 70 to 100 parts by mass of component (I). It can obtain by mix | blending 120 mass parts and condensation reaction. When the compounding quantity of (II) component is less than 1 mass part, and when it exceeds 200 mass parts, the adhesiveness of the hardened | cured material obtained is impaired.

As described above, when the component (II) is used instead of the organic solvent when the component (I) is prepared, the condensation reaction between the component (I) and the component (II) is also terminated at that time. Therefore, in this case, when the compounding quantity of (II) component at the time of (I) component manufacture exists in the said range, it is not necessary to add another (II) component to (I) component after manufacture.

It is preferable to use a condensation reaction catalyst in condensation reaction of (I) component and (II) component. Although a titanium compound, a tin compound, an amine compound, an alkali metal compound, etc. are mentioned as a condensation reaction catalyst, It is preferable to use an amine compound. Specific examples of the amine compound include ethylamine, propylamine, isopropylamine, butylamine, diethylamine, dibutylamine, triethylamine, and ammonia water.

Although the compounding quantity of a condensation reaction catalyst can be made into an effective amount as a catalyst, Although it does not restrict | limit especially, Usually, what is necessary is just about 0.05-3.0 mass parts with respect to a total of 100 mass parts of (I) component and (II) component.

Although condensation reaction temperature is not specifically limited, Usually, it is good to set it as 1-120 degreeC, Preferably it is 10-80 degreeC. Although reaction time is not specifically limited, either, about 0.5 to 12 hours.

After completion of the condensation reaction, the solvent and / or unreacted organopolysiloxane, diorganopolysiloxane, condensation reaction catalyst and the like may be distilled off as necessary. Furthermore, in order to adjust the viscosity of a condensation reaction product, low molecular cyclic siloxanes, such as organopolysiloxane or octamethylcyclo tetrasiloxane which the terminal was sealed by the trimethylsiloxy group, a vinyl group, etc .; Aliphatic hydrocarbons; Aromatic hydrocarbons; Liquid paraffin: isoparaffin; Photoreactive diluents, such as an acrylate ester, can also be added. As such a viscosity adjustment component, it is effective to use a thing with a viscosity in 23 degreeC about 5 to 1,000 mm <2> / s.

[Component (B)] [

Component (B) imparts ultraviolet curability to the composition of the present invention, and is incorporated into, for example, an organopolysiloxane serving as a base by a condensation reaction to provide stable ultraviolet curability.

(B) component is the (meth) acryl functional alkoxysilane represented by following General formula (1).

&Lt; Formula 1 >

(Wherein R ¹ is a hydrogen atom or a methyl group, R ² is a divalent organic group, R ³ and R ⁴ are the same or different unsubstituted or substituted monovalent hydrocarbon groups, respectively, a is an integer of 0 to 2).

As R <^2> , an alkylene group can be illustrated, for example, A C1-C6 alkylene group is especially preferable. Moreover, as a specific example of R <^3> and R <^4> , Alkyl groups, such as a methyl group, an ethyl group, a propyl group, a butyl group; Aryl groups, such as a phenyl group, are mentioned, It is preferable that carbon number of these groups is 1-8. In addition, R ³ is not an essential group.

Specific examples of the component (B) can be exemplified by the compounds represented by the following general formulas, but are not limited thereto.

In addition, (B) component can also be used individually by 1 type or in combination of 2 or more type as long as it corresponds to General formula (1).

It is preferable that the compounding ratio of (B) component in the composition of this invention shall be 1-50 mass parts per 100 mass parts of (A) component, and may be 5-30 mass parts. When the compounding ratio of (B) component is less than 1 mass part, the ultraviolet curability of a composition will fall, and when it exceeds 50 mass parts, only a (B) component will harden | cure, and a problem arises that adhesiveness is impaired.

[Component (C)] [

(C) component is a catalyst for condensation reaction which selectively advances the condensation reaction of the silanol of (A) component and the alkoxy group of (B) component.

As (C) component, well-known catalysts, such as an organic tin ester compound, an organic tin chelate compound, an alkoxy titanium compound, a titanium chelate compound, an organoaluminum compound, an organic zirconium compound, the silicon compound which has a guanidyl group, an amine compound, are mentioned. have.

Specific examples of the component (C) include tin octoate, dimethyl tin diversate, dimethyl tin dioctoate, dibutyl tin dioctoate, dibutyl tin dilaurate, dioctyl tin dioctoate, and dioctyl tin di. Laurate tetrabutyl titanate, tetraisopropyl titanate, diisopropoxybis (acetylacetonate) titanium, diisopropoxybis (ethylacetoacetate) titanium, aluminum tris (acetylacetonate), aluminum tris (ethylaceto Acetate), zirconium tetra (acetylacetonate), zirconium tetrabutylate, hexylamine, dodecyl phosphate, tetramethylguanidinepropyltrimethoxysilane, although not limited thereto.

In addition, (C) component can also be used individually by 1 type or in combination of 2 or more type.

The compounding ratio of (C) component in the composition of this invention is 0.01-10 mass parts per 100 mass parts of (A) component, Preferably it is 0.1-5 mass parts. If the blending ratio of the component (C) is less than 0.01 parts by mass, the capacity as a catalyst is not sufficiently exhibited. If it exceeds 10 parts by mass, problems such as poor storage stability of the composition occur.

[Component (D)] [

(D) component is a photoinitiator required in order to ultraviolet-cure a composition. As the component (D), for example, benzoin and its derivatives, benzoin ethers such as benzoin acryl ether, benzyl and its derivatives, aromatic diazonium salts, anthraquinone and its derivatives, acetophenone and its derivatives, di Sulfur compounds, such as phenyl disulfide, benzophenone and its derivatives are mentioned, but it is not limited to this.

In addition, (C) component can also be used individually by 1 type or in combination of 2 or more type.

The compounding ratio of (D) component in the composition of this invention is 0.01-10 mass parts per 100 mass parts of (A) component, Preferably it is 0.1-5 mass parts. When the compounding ratio of (D) component is less than 0.01 mass part, the capability as a photoinitiator will not fully be exhibited, and when it exceeds 10 mass parts, problems, such as the adhesiveness of a composition fall, arise.

[Other Ingredients]

In addition to the above-mentioned (A)-(D) components, the composition of this invention can also mix | blend a generally well-known filler, an additive, etc. as needed. Examples of the filler include pulverized silica, fumed silica, calcium carbonate, zinc carbonate, wet silica and the like. In addition, thixotropy improvers such as polyethers, antibacterial agents, antibacterial agents, and the like can also be blended.

[Preparation of composition]

After adjusting the said (A) component, the composition of this invention adds (B)-(D) component, Preferably it can manufacture by mixing these in the state of anhydride.

<Application of the composition of the present invention>

The composition of this invention can be used suitably as a sealing compound for flat panel displays, and it is preferable to use it especially for the sealing of flat panel display elements as shown in FIG.

In FIG. 1, the flat panel display element is comprised by bonding the glass substrate 2 and the film circuit (TCP: Tape Carrier Package) 8 with the anisotropically conductive adhesive agent (ACF) 10. In FIG. The display image part (for example, the pixel of a liquid crystal in the case of a liquid crystal display) 6 is formed in the center part of one side of the glass substrate 2, and it is strip-formed from the display image part 6 toward the edge of a glass substrate. The electrode 4 is extended. The electrode 4 usually consists of a transparent electrode such as ITO (indium tin oxide), and loads a voltage on each pixel by controlling the driving circuit to turn each pixel on and off. An alkali free glass and quartz glass can be used suitably as a glass substrate.

The film circuit 8 connects the transparent electrode 4, the drive circuit which is not shown in figure, and an external power supply, and is a flexible circuit which covered the copper foil circuit and IC with polyimide film or another resin, for example.

The sealing agent for flat panel displays of this invention can seal effectively the part which makes the glass substrate 2, the (transparent) electrode 4, and the film circuit 8 into the sealing area 20 as mentioned above, It is excellent in both adhesiveness and mold release property with respect to these raw materials (glass, a (transparent) electrode, and the film of a film circuit).

<Examples>

Although an Example is given to this invention below, this invention is not limited to these examples. In addition, "part" and "%" shown in an Example represent a mass part and mass% unless there is particular notice.

&Lt; Example 1 >

Preparation of (A) component: The 4-necked separation flask equipped with a thermometer, a stirring rod, a reflux condenser, and a nitrogen introduction tube was nitrogen-substituted. Subsequently, (I) as the component (CH ₃₎ in a molar ratio represented by ₃ SiO _1/2 units and SiO _4/2 is made of a _{unit, {(CH 3) 3 SiO} 1/2 units _/ SiO _4/2 units} 0.74, and an organopolysiloxane having a hydroxyl group content of 1.62% by weight bonded to a silicon atom was prepared. It dissolved in toluene so that solid content of (I) component might be 50 weight%. Both terminal silanol group-blocked dimethylpolysiloxanes having a viscosity of 20000 mm 2 / s as a component (II) at 23 ° C with respect to 100 parts of component (I) (100 parts of the toluene solution as a whole and 50 parts of component (I) alone in toluene). 50 parts of was added, and stirred and mixed uniformly, 0.5 part of ammonia water was added dropwise, and condensation reaction was performed at 20 ° C for 3 hours. Subsequently, toluene and low molecular weight by-products were removed, heating this to 120 degreeC, and it adjusted so that solid content might be 50 weight%, and obtained (A) component.

Preparation of a composition: 20 parts of (B) component (methacryloxypropyl trimethoxysilane) with respect to 150 parts of said (A) component, 0.5 part of (C) component (tin octoate), (D) component (diethoxyaceto 2 parts of phenone) was combined to prepare a composition.

<Example 2>

The composition was obtained in exactly the same manner as in Example 1 except that 0.1 part of dioctyl tin dilaurate was added instead of tin octoate as the component (C).

<Example 3>

Preparation of component (A): (A) Component was carried out similarly to Example 1 except having added 50 parts of both terminal silanol group blocking dimethylpolysiloxanes whose viscosity in 23 degreeC is 700 mm <2> / s as (II) component. Got.

Preparation of composition: Except having used this (A) component and mix | blended 20 parts of acryloxypropyl trimethoxysilane instead of methacryloxypropyl trimethoxysilane as (B) component, it was exactly the same as Example 1. To obtain a composition.

<Example 4>

Preparation of (A) component: (A) Component was obtained like Example 1 except having changed the compounding quantity of (I) component into 60 parts and changing the compounding quantity of (1I) component to 70 parts.

Preparation of composition: Except having mix | blended 130 parts of this (A) component instead of the (A) component of Example 1, the components were mix | blended similarly to Example 1, and the composition was obtained.

<Example 5>

The compounding quantity of (B) component (methacryloxypropyl trimethoxysilane) was changed to 10 parts, and (C) component is a combination of 0.3 part of dioctyl tin dilaurate and 3 parts of tetraisopropyl titanate instead of tin octoate as a component. Except having mix | blended, it carried out similarly to Example 1, and obtained the composition.

&Lt; Comparative Example 1 &

Preparation of (A) component: (A) Component was obtained like Example 1 except having not mix | blended (I) component, and changing the compounding quantity of (II) component to 100 parts, and not dropping ammonia water.

Preparation of composition: Except having mix | blended 100 parts of this (A) component instead of the (A) component of Example 1, the components were mix | blended similarly to Example 1, and the composition was obtained.

Comparative Example 2

Preparation of (A) component: After uniformly stirring-mixing (I) component and (II) component, it carried out similarly to Example 1 except having heated to 120 degreeC and removing toluene, without dropping ammonia water (A ) Component was obtained. Instead of the component (A) of Example 1, the components (B) to (D) were blended in the same manner as in Example 1 except that the component (A) in which 150 parts of the component (A) was blended was used to obtain a composition. .

&Lt; Comparative Example 3 &

Except not having mix | blended (C) component, it carried out similarly to Example 1, and obtained the composition.

&Lt; Comparative Example 4 &

Preparation of (A) component: (A) Component was obtained like Example 1 except having not mix | blended (I) component, and changing the compounding quantity of (II) component to 100 parts, and not dropping ammonia water.

Preparation of Composition: Except for using 100 parts of this (A) component and 1 part of 3-glycidoxypropyltrimethoxysilane (adhesive aid) instead of the component (A) of Example 1, The composition was obtained by mix | blending B)-(D) component.

<Evaluation>

Each obtained composition was molded into a sheet having a thickness of 3 mm, and cured at 23 ± 2 ° C. under an environment of 50 ± 5% RH for 1 day, and then a high pressure mercury lamp (80 W by a Nippon Denshi Co., Ltd. conveyor type). / cm) was cured by ultraviolet irradiation three times at a distance of 10 cm and a speed of 1 m / min. Its rubber properties (hardness and tensile strength) were measured.

Moreover, each composition obtained separately from this was apply | coated in 1 mm thickness on glass, and the mold release property and adhesiveness with respect to the glass of what hardened | cured on the conditions similar to the above were evaluated.

(1) hardness

Durometer hardness A (Duro.A) of hardened | cured material was measured based on JISK-6253.

(2) tensile strength

Tensile strength (MPa) of hardened | cured material was measured based on JISK-6251.

(3) release property and adhesion

It judged by the following references | standards.

Adhesive: Inability to simply peel off the cured product from the glass

No adhesion: able to simply peel off the cured product from the glass

With release property: No hardened material left on the glass surface

No release property: hardened material left on the glass surface

The obtained results are shown in Table 1 below.

As is apparent from Table 1, in each example, the rubber physical properties (hardness and tensile strength), mold release property and adhesion of the cured composition were all excellent.

On the other hand, in the comparative example 1 in which (I) component was not mix | blended with (A) component, all the hardness, tensile strength, and adhesiveness of hardened | cured material fell.

In the comparative example 2 in which (I) component and (II) component were simply mixed without condensing in (A) component, although the hardness of hardened | cured material was high, both tensile strength and adhesiveness fell.

In the comparative example 3 which did not mix | blend (C) component, each component in a composition did not condense and the hardness, tensile strength, and adhesiveness of hardened | cured material were inferior.

In the case of the comparative example 4 using an adhesive agent as a sealing agent, all the hardness, tensile strength, and mold release property of hardened | cured material fell.

<Example 6>

About the actual product of the liquid crystal display shown in FIG. 1, the composition of Example 1 was sealed to the seal | sticker area | region 20 and hardened. Then, when the mold release property and adhesiveness were evaluated by the method similar to the above, all were excellent.

According to the present invention, a curable organopolysiloxane composition is obtained, which is cured under room temperature and ultraviolet irradiation, and has a good storage stability and can form a cured product having good adhesion and release property to glass, metal, plastic and the like. This invention is especially suitable for the coating agent and flat plate sealing agent of an electrical / electronic component or a circuit.

Claims (7)

(A) 100 parts by mass of the organopolysiloxane as a condensation reaction product of 100 parts by mass of the following (I) component and 1 to 200 parts by mass of the component (II), Component (I) is a repeating unit of R ₃ SiO _1/2 unit (wherein R each independently represents a monovalent hydrocarbon group having 1 to 6 carbon atoms of unsubstituted or halogen atom substitution) and SiO _4/2 unit and a and, SiO _4/2 units, and the ratio of R ₃ SiO _1/2 units to 1 mol of 0.5 to 1.2 mol, organosiloxane having a hydroxyl group bonded to a silicon atom is less than 6.0% by weight polysiloxane, Component (II) is diorganopolysiloxane whose molecular chain ends are blocked with functional group-containing silyl groups; (B) 1 to 50 parts by mass of (meth) acryl functional alkoxysilane represented by the following formula (1), (C) 0.01 to 10 parts by mass of a catalyst for condensation reaction, and (D) Curable organopolysiloxane composition containing 0.01-10 mass parts of photoinitiators. &Lt; Formula 1 >

(Wherein R ¹ is a hydrogen atom or a methyl group, R ² is an alkylene group having 1 to 6 carbon atoms, R ³ and R ⁴ are the same or different unsubstituted monovalent hydrocarbon groups having 1 to 8 carbon atoms, a Is an integer from 0 to 2) The method according to claim 1, wherein component (I) is based on 1 mole of SiO _4/2 units, wherein R ₂ SiO _2/2 units and RSiO _3/2 units (wherein R is each independently unsubstituted or substituted with a halogen atom) Curable organopolysiloxane composition which has one or more of each C1-C6 monovalent hydrocarbon group) so that each unit may be 1.0 mol or less, and the sum total of each unit may be 1.0 mol or less. The curable organopolysiloxane composition according to claim 1 or 2, wherein the component (II) is a diorganopolysiloxane represented by the following formula (2). (2)

(Wherein R ⁵ is each independently an unsubstituted or halogen-substituted monovalent hydrocarbon group having 1 to 10 carbon atoms, X each represents a hydroxy group, an alkoxy group, an alkoxyalkoxy group, an alkenyloxy group, a ketoxime group, an acyl jade) Independent functional group selected from time period, aminooxy group, amino group and amide group, a is an integer of 1 to 3, n is an integer of 10 or more) The sealing compound for flat panel displays containing the curable organopolysiloxane composition of Claim 1 or 2. The sealing compound for flat panel displays containing curable organopolysiloxane composition of Claim 3. The flat panel display element which used the sealing compound for flat panel displays of Claim 4 for the sealing of the area | region containing the electrode on the glass substrate of the said display, and the film circuit connected on this electrode. The flat panel display element which used the sealing compound for flat panel displays of Claim 5 for the sealing of the area | region containing the electrode on the glass substrate of the said display, and the film circuit connected on this electrode.

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